Metalation reactions-XIV. The generality of the 1.3-Sigmatropic shift of hydrogen in allenyllithium compounds

J. Klein, J. Y. Becker

Research output: Contribution to journalArticlepeer-review

43 Scopus citations

Abstract

Dimetalation of aliphatic 2-alkynes was observed in mild conditions in ether solution. Only 2-butyne has undergone monometalation exclusively. The dilithio compounds of 1- and 2-alkynes were attacked by electrophiles first at the 3-position. A 1.3-sigmatropic shift occurred in the monolithioallenes to give terminal acetylides. Metalation of 3-alkyne gave only a monolithiated compound in the conditions studied.

Original languageEnglish
Pages (from-to)5385-5392
Number of pages8
JournalTetrahedron
Volume28
Issue number21
DOIs
StatePublished - 1 Jan 1972
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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